


The SissyBoy Sagas

by Kono10



Series: The SissyBoy Sagas [1]
Category: Original Work
Genre: Age Play, Anal Sex, Bears, Comedy, Cross-Generation Relationship, Daddy Kink, Explicit Sexual Content, Gay, Gay Sex, Girly boys, Horny Teenagers, Implied/Referenced Incest, M/M, Older Man/Younger Man, Oral Sex, Other, Porn, Rimming, Satire, Sexual Fantasy, Shameless Smut, Sissies, Slutty boys, Smut, Sugar Daddy, Teenagers, Twinks, Underage Sex, Urban, Yaoi, chapters, saga
Language: English
Status: In-Progress
Published: 2019-09-14
Updated: 2019-10-26
Packaged: 2020-10-18 10:09:58
Rating: Explicit
Warnings: Underage
Chapters: 4
Words: 12,479
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20637434
Author URL: https://archiveofourown.org/users/Kono10/pseuds/Kono10
Summary: Meet Quintan Kubiack! A 17 year old sissyboy wannabe on a desperate mission to become a sissyboy idol on SissyBoy.net and find himself a rich daddy before his 18th birthday! However, he's gonna learn that he's got a long way to go and a lot to learn about the competitiveness of the world of sissyboys. Will Quinn become an idol and find himself a handsome rich daddy?Find out by stepping into the world of sissyboys in this satirical, raunchy, and inappropriate collection of stories about teenage gay sex, pretty clothes, and the people that love it all!





	1. Quintan, the Rising Sissyboy Idol!

Quintan Kubiack had a confession to make.

He was a…a….sissyboy!

Gasp!

Well..

It wasn’t a confession. Just his daily public declaration. Positive affirmation, one could call it.

He told just about everyone almost every day since he first discovered five years ago at the tender age of 12 that he, himself, was a sissyboy. He really didn’t need to tell people that he was a sissyboy because it was obvious.

He loved wearing sissy clothes such as pretty nighties, mini shorts (the tighter the better!), skin-tight shirts, and midriff blouses on his slim schoolboy frame. He couldn’t get enough of cotton, silk, and lacey panties on his full bubble butt, and simply adored platform shoes, strappy sandals, and kitten heels on his pedicured toes.

Everything!

He treasured bright, sissy, makeup to enhance his big brown eyes along with dark, dramatic, mascara to make his long girlish lashes stand out. He applied the glossiest of glosses to make his lips look extra plump, and he styled his fluffy, shiny, brown curls to frame his face, making him look like an exotic doll.

He loved it all!

He even acted sissy. You couldn’t catch him doing anything that would get his nice sissy clothes dirty or ruin his expensive mani-pedi.

Even though he didn’t realize his sissy potential until he was 12, he believed that the sissy gene had always been in his blood.

It must have come from his mother.

Before she ran off with a millionaire Nas-car driver when he was 6, Quinn knew she was a beautiful, high maintenance wife to his father. His mother was a pretty Haitian woman originally from Los Angeles who obviously didn’t belong in the stupid redneck town of Rawhide, East Texas that he was currently stuck in with his father. Her curvaceous body, long, relaxed hair, and plump bosom got the attention of everyone around her. She could have gotten any man she wanted, but what made her come to that town and choose his country-bred, brutish, father as a husband was the mystery of his life.

Quinn hated that town. He grew up there along with his daddy, but now he was ready to leave. There was nothing to do in the town, only disgusting dirty things like BBQs, mudding on four wheelers, riding horses, or tailgating.

Ugh!

This boring barbaric town stood in his way of finding a proper rich daddy. After high school, he was taking a plane to LA, New York, or Manhattan, and securing himself a meal ticket just like his mother! 

He still saw her on tv sometimes, standing next to that blonde haired, blue eyed, handsome, fit, rich, God of a man, looking as happy and gorgeous as ever.

Quinn couldn’t blame her! He’d run off from his redneck, not so handsome, and not so rich, father too!

His daddy was a dirty oil field worker for 20 years who made only a meager $90,000 a year (not including holiday bonuses and over time). Sometimes when Quinn looked at his father’s tall and heavy-built body slouching over in his dirty work coveralls with his unkempt hair and beard framing his long, grumpy face, he couldn’t help but pray that perhaps his mother had cheated on his father before he was born and got pregnant with him by another man (hopefully a richer and more distinguished one).

Not that Quinn didn’t love his father.

Of course, he did. All sissyboys loved their real daddies. Sometimes it went deeper than the typical paternal father/son love. It did for many sissyboys on SissyBoy.net. Even Quintan sometimes. His father wasn’t mean nor was he entirely ugly, just a brutish, rugged man with no sense of refinement or style. Unlike the hot classy man in the designer suit his mother ran off with or the ones the other boys on SissyBoy.net had.

He loved daddy. He even suggested they bond more intimately like some of the boys on the site did with their daddies and stepdaddies. It wasn’t strange to Quinn. Boys bonded with their daddies all the time, whether it be throwing balls around or taking them in their mouths.

Quinn saw no difference.

Either his daddy ignored his suggestion or didn’t understand.

When he came out to daddy at the age of 12, revealing to him that he was a…a…sissyboy! With a slow head shake of part shame and part cluelessness, daddy accepted his sissyboy son.

That goes to say that Quintan wasn’t always a sissyboy.

A long long time ago (a time Quinn would rather not remember), he was a dirty, rough, hetero little non-sissyboy with an unrefined palate and a vulgar, improper vocabulary like the rest of the bumpkin boys in his East Texas town.

In those forgotten times, he hadn’t discovered the joys of wearing sissy panties, thigh highs, and rouge.

In those dark barbaric times, all Quinn cared about was playing outside in the dirt and mud.

Gag!

Or catching beetles and fuzzy caterpillars with his friends!

Retch!

And playing CONTACT sports with the other dirty street urchins around his neighborhood.

Ugh!

What was he even thinking? Never again, not with his pretty mani/pedi, soft skin, and delicate frame.

His life changed for the better on one fateful afternoon.

A little after his 12th birthday, his father took him to the store to get some new clothes for the school year (Something he hated, but now he loved more than anything!). While passing through the girls’ clothing section, Quinn found a small pair of cotton white panties with pretty blue stripes on them on.

Little Quinn was so intrigued by the tiny piece of intimate fabric that he slipped them into his pocket and decided to take them home.

That night-

as a joke of course-

Quinn slipped the panties on over his skinny legs and butt.

Haha! How dumb!

Boys in girls’ panties!

How gay!

How ridicu-

Oh.

Oh my.

Quinn was surprised at how soft the cotton felt on his bum. They felt nothing like the thick cotton of his Teenage Mutant Ninja Turtles undies! These little panties were comfy, yet they squeezed his nether regions just right.

He looked at himself in the mirror and was surprised at what he saw.

These panties looked absolutely amazing on him. The white contrasted against his dark skin, the stripes were innocent and cute, and made his legs look long and pretty. He twisted and turned around to check out his butt and was not disappointed at what he saw. Then he bent over to see his boy package tucked snuggly underneath.

He looked good in panties.

No.

Tantalizing. (Where did that word come from?)

Or dare he even say…sexy?

Oh.

Well.

Something unusual happened then. Quinn got an erection. This was new. His first conscious erection from looking at himself in the mirror in a pair of stolen girls’ panties.

What should I do? He wondered while staring at his tented panties.

He did the only thing he could think of.

He played with his teeny weeny hard peeny through his stripy peenties.

He watched himself play with himself. Damn he was cute! This was the strangest, hottest thing he had ever seen in all his 12 years!

He- he wanted more undies like this. More clothes like this. Stripy, colorful, pretty, clothes like these!

He wanted people to see him in panties!

But what girl wanted to see a boy in panties?

He tried to search for an answer to this odd question on the all-knowing world wide web where he shortly learned that no girls wanted to see him in panties, but PLENTY of men did.

What? Men did? Why? Men can’t like boys.

Can’t they?

That’s illegal!

Well, Quinn did just steal a single pair of panties, but it wasn’t the same!

After perusing the interwebs more, he quickly found out that they can like boys, and they do!

Quinn liked this idea! Men the same age as his daddy admiring him in his panties. That idea kept him up at night for weeks with sexy thoughts and he decided that he liked men and wanted them to like him too!

But he needed more panties! How could he get them? While perusing the interwebs once more, he found SissyBoy.net.

Sissyboy? What the heck was that?

He clicked on the site and was immediately blinded by bright pink colors and diamonds and hearts and other girly designs.

_Welcome to SissyBoy.net! The social media sensation for all the sissyboys of the world and the men who love to adore them. All the sassiest of sissyboys have an account on our site! If you’re a saucy sissy looking for some extra saucy clothes, then head over to our sister site SissyBoyMerch.net and get daddy to fill your lovely closet with all the latest sissyboy fashions! If you’re a sweetie boy who loves to show off your goods, or a man looking for your very own sissy, then sign up today! _It said.

Quinn couldn’t fathom such a site! Everywhere there were pictures of the most prettiest boys he had ever seen, and they were in scanty girls’ clothes! He didn’t know boys could be so pretty! He scrolled and found that most of these boys were teenagers who were already in relationships with MEN.

Woah!

These boys were gaining popularity and becoming famous. There were even top 10 idols that rotated every year.

Amazing!

They posted pictures of themselves with their older handsome boyfriends doing….naughty things.

Blush!

Quinn was stunned! It all scared him at first, but the more he scrolled and saw that all these boys looked like they were having the time of their lives, his fear turned into excitement and enthusiasm. He wanted to do all this too!

These men wanted nothing but boys in panties and short shorts, lacey nighties, and frilly dresses. These rich, hot, classy men! He wanted one of these men. He wanted to be like these pretty boys! He wanted to be a sissyboy!

While scrolling through the plethora of gossip blogs, profiles, videos, and photos of boys doing…ahem...sexual things with men, Quinn had his first ever orgasm (It was dry of course, but he would have plenty wet ones in the next 5 years).

Quinn felt like he found his calling in life!

No.

He was already a sissyboy. It was just time to embrace it!

That’s when he spiraled down the sissyboy rabbit hole.

He used his daddy’s credit card to sign up for a premium account, allowing him to access to exclusive merch, fashions, and inside information on where to find hot daddies in his local area.

He tossed out his nasty old toys, and had his daddy take out all his pet bugs, and with his allowance he stocked up on all things sissy to redecorate his room.

He fixed his vernacular and no longer spoke like an East Texas backwoods hick like everyone else (However, when Quinn got angry or overwhelmed, his improper old ways tended to show themselves without his consent, but don’t you dare tell Quinn if he’s doing it!).

He was ready to be 100% undeniably sissified.

At 14 years old, he already accumulated over 300 fans (even though he did nothing but lurk on other profiles, and occasionally post pics of himself in a new pair of panties or some new outfit on the site). He stalked the top 10 idols’ pages, gaining tips from the more experienced sissies, waiting for his chance to make his full debut and become a rising idol on the site.

Three years and more than 5,000 fans later, Quinn was ready to make his breakout debut and become an idol.

Except for the only thing that made those boys the top idols was the fact that they all had hot rich daddies.

Quinn had nothing.

So now Quintan was ready to embark on his quest to snag a rich husband… but there were two slight problems that were holding him back.

First, he was a virgin.

At 17, he was still a virgin sissy. Not counting toys and such, he had never had a real flesh and bone…bone inside of him. Unlike those bragging cunts on SissyBoy.net who flaunted their relationships with their rich daddies, posting pics of their post-sex silk sheets or on their knees in front of their daddies, who were petting their heads with big Rolexes on their wrists, or their sissy bodies blanketed in daddy cum.

Quin was on fire with envy. He wanted a daddy with a Rolex! He wanted to post pictures of his dirty fuck sheets and pictures of himself drowning in daddy cum!

He needed to hurry up and lose his cherry before he turned 18 next month because a sissyboy who didn’t have their first daddy by 18 was considered a loser. He’d be a laughingstock of SissyBoy.net!

Which brought him to his next problem.

Why weren’t any grown men trying to bang him?

What the hell?

He thought men lined up for sissyboys!

He quickly learned that the men on SissyBoy.net were just a bunch of lurking, lying, cowards who always said they had money and wanted to wine and dine him, but at the mention of meeting up, they flaked.

Pussies!

Who knew the internet could be so deceitful!

_This shit is ridiculous!_ Quintan thought as he gussied himself up in his vanity mirror, reapplying his strawberry lip gloss and readjusting his favorite sheer white babydoll nightie.

What did those dicked-down sissies on the internet have that he didn’t?

Was he too old now? Did he waste too many of his prime years lurking and being a chicken, making it too late to find him a man?

He did read somewhere that most men only went after the younger sissies.

Sick perverts!

Where were the sick perverts that perved on 17-year olds?!

That couldn’t be it. There were some older boys on the site that got plenty of attention. One of the top 10 idols that had been an idol three years in a row, was actually 21 years old, but even he was considered a veteran.

Was he not sissy enough?

He looked around his pink and purple room that he decorated over the years with pretty things from SissyBoyMerch.net. He looked good in frills, lace, babydoll clothes, stockings, leather harnesses, and panties!

He was hairless too.

Mostly.

Damn puberty, making his legs and butthole hairy which he made sure to get waxed at the first sight of stubble.

_Sissy knows no pain_. He always told himself every 4 weeks when it was time for a touch up and his waxer ripped the hairs from his asshole.

Was he an ugo (ugly person)?

Unlikely!

Thanks to his mommy and daddy’s coffee and milk union, he was what the sissies in the forums called a ‘mixed breed’. People always liked those! He was considered exotic. A walking fetish!

He had flawless brown skin. Beautiful girlish lashes that bitches would kill for, and slutty plump lips. Perfect for sucking dick! They were made for it!

Was his tight, round, brown ass not tight and round and brown enough?

Also unlikely.

He could cinch a metal pipe shut with his ass cheeks, they were so tight!

He continued to gaze at himself in the mirror, letting his fingers glide down his body then stopped to give his hard nippies a massage through the sheer fabric of his nighty.

Quinn was just being paranoid. Of course men wanted him! No one could resist him!

Even he couldn’t resist himself at times!

He gave himself a naughty wink then leaned in for a nice lusty kiss, leaving a glossy lip stain on his mirror. He made out with himself as he felt the front of his panties grow tighter.

_Oh, mercy me._ Quinn giggled.

Another erection whilst looking at himself in the mirror?

What a conceited little bitch he was!

He pulled his little white stringed panties down to his mid thighs and stroked his pretty little penis. It was a pretty brown color, but its tip was a naughty shade of blush pink, and his balls underneath were as soft as a satin pouch.

Sigh.

If only he had a proper daddy to do this for.

He could only imagine now. Daydream. Fantasize about a man bending him over his vanity and thrusting his man meat in and out of his longing virgin hole.

Quinn always masturbated to the fantasy of his first time.

Picture it.

He’s walking down the aisle, getting ready to marry a man. The man was tall, maybe 35-40. Handsome. Blond haired. Blue eyed. Smooth talking. Filthy rich.

Oh!

Quinn’s wedding dress was breath-taking and white and frilly with a long train in the back but short in the front, showing off his long legs and just barely covering his pure white lacy panties. His husband, looking ready to ravish him, gives him a 25-carat diamond ring then sweeps him off his feet to their honeymoon suite. His new husband-daddy lays him down on a bed of sheets made of Egyptian cotton or something, kissing and admiring him like the princess he was.

“You’re the most beautiful boy I’ve ever seen. Your wish is my command.” His husband whispered to him.

“Make love to me!” Quinn throws his arms around his gorgeous husband.

They embrace passionately then his husband makes love to him with abandonment. His long and thick penis sending Quinn to higher heights. But before Quinn could finish his fantasy, he was shaking and spurting his sissy cream all over his vanity mirror.

It was such a magnificent fantasy, but even after relieving himself, Quinn usually got even more frustrated than he was before.

Dammit, he wanted a daddy more than anything! He’d give his left nut for one!

However, he didn’t have to sacrifice his pretty left nut just yet because he recently came across some valuable information about how he could snag a daddy before his birthday next month.

A few nights ago, Quinn was stalking the profiles of some of the local sissies around his town (He didn’t associate with them because they were pretty top-tier, and he didn’t like to be outshined in a group!). Most of them were rich, had daddies, and attended private school anyways which didn’t make his situation any better because he had to attend….a….a…public school.

Gag!

They were talking about an event that was gonna be held the night before his birthday at the DaddyFatStacks Private Country Club in the north swanky part of the city. The club was located on a 190-acre park with a huge golf course, private luxury spas, gourmet chefs, and a grotto where men and their sissies lived happily ever after. They said every year the club held a “beauty pageant for young men” where at the end, wealthy men from across the state would auction for the top contestants, and the proceedings went to “charity.”

All those daddies! All that money! Quinn needed to be there! His radiant beauty would dominate all those other boys, and men would be chunking money at him!

He needed a way in, but access was super exclusive, so the only plausible idea he could think of was talking to…him…the son of the club’s owner.

Known for his fairytale beauty and innocent look, he was named the “Golden-haired sweetheart” of SissyBoy.net, aka, Goldilocks.

He was a 17yo, top 5 idol, and he was on the home page of SissyBoy.net a year ago. Goldilock’s husband-daddy was James Texarkana, the second richest oil tycoon in East Texas. Both of his daddies were two of the richest men in East Texas. His real daddy owned the oil drilling company Quinn’s own daddy worked for! That made Quinn grind his teeth.

He didn’t want to talk to him, but dammit he wanted to get in that pageant!

So, he sucked up his pride, and without trying to sound too desperate, he shot the idol a message, inquiring about how he could participate in the auction.

To Quinn’s delight, the boy finally responded to his message that night and told him he would try to help, but Quinn had to stop by his house first for an interview next Friday.

An interview? What the hell was he supposed to be doing? Plus, his house was a two hour drive out of town! But now was not the time for Quinn to be backing out.

His plan was finally setting into motion, and he was finally gonna get himself a husband-daddy before his birthday. No more Rawhide, Texas! No more shopping in the clearance section of SissyBoyMerch.net! He was gonna become a rich idol and live the life he deserved!


	2. Quinn Meets a True Idol!

**Summary for the Chapter:**

> Quinn meets SissyBoy.net's top 5 idol, Goldilocks!

Quintan’s taxi pulled up that Friday afternoon at the iron gates of an all-white, three-story mansion. Quinn made sure to look his best in his business casual, mid-thigh, khaki shorts that showed off his smooth brown legs, along with a form fitting, button up, white shirt to hug his lean frame, and a pair of black and white saddle oxfords to complete the look. His outfit was business enough for the interview yet still arousing enough to catch attention. Even his taxi driver gave him a few suggestive backwards glances.

_Not a chance, peasant!_ Quinn turned his nose up at the cabby.

The Texarkana mansion was insanely lavish!

HE was the one who deserved to live in a palace like this!

The servants let him inside the mansion’s sitting room where he waited almost an hour and a half before Goldilocks arrived, pulling up in a fancy sports car.

“I apologize for being late, and I look such a mess.” Goldi’s low sultry voice purred, and an elegantly pure smile shone brightly on his angelic face. “I had to stay a little late at school.”

Quinn was at a loss for words. He had seen Goldilocks on SissyBoy.net before and admittedly, he was beautiful, but seeing him in real life was on a whole other level. He really was fairytale gorgeous!

Just as his name sake, he had glossy, blonde, shoulder-length ringlets, dazzling sapphire eyes, and his porcelain skin was flawless like a figure in a classical painting. His tight private school uniform was fitted to his angular body, and the super tiny plaid shorts squeezed against his ample bottom. He brushed his golden curls from his face, and the huge diamond rock that sat on his slim milky finger blinded Quinn in the light.

Quinn could see why he was a favorite on SissyBoy.net! This was a true idol!

“I’m gonna go put my stuff upstairs. Please let me show you around.” Goldi turned up the stairs, and Quinn reluctantly followed him, trying not to gawk at the picturesque mansion interior.

While walking the halls, Goldi casually noted about the rooms and furniture.

“Daddy bought this couch last year on our winter vacation in France.” He said while pointing to a very Avant Garde style couch. “It’s just ever so my favorite piece in the whole house.”

“This room is where Daddy keeps his trophies and guns. He’s a big game hunter. Every year, he goes to Africa or Asia and comes back with lion pelts, bear skins, or ivory. Even though I’m totally against hunting wildlife, but no one can tell daddy what to do.”

“This room is daddy’s office. He’s always working so hard. I can’t even count on my hands and feet how much money he makes. Oh well, as long as he gives me stuff, I don’t care.” He let out an adorably childish giggle that made Quinn’s knees go weak, but at the same time, he was trying his best to hide his bitterness.

“And this is where all the magic happens.” Goldi opened a door to the biggest most luxurious bedroom Quinn had ever seen. “This is daddy and I’s bedroom. I have three rooms of my own, but he doesn’t allow me to sleep in them. Only with him.” The beautiful blonde blushed coyly.

Quinn recognized those sheets and blankets from some of the pictures on Goldi’s profile.

Goldi’s bedroom was no less than amazing as well. Filled with lavish furnishings, an exercise pole, a princess canopy bed with all the comforts and décor from the expensive, high-end section of SissyBoyMerch.net (A section that Quinn could only dream of shopping from). By the end of the house tour, Quinn was nauseas with jealousy.

“Let’s go chat by the pool. I’ll have the servants bring us some imported Japanese green tea and sweets.” Said Goldi.

They went to Goldi’s backyard where it had a built-in lounging deck, an in-ground pool, and an indoor and outdoor hot tub. 

“Please, sit.” He motioned to a pool chair next to him and Quinn obediently sat while the servants served them tea. “So, please tell me a little about yourself...” Goldi grinned angelically.


	3. Interview with Goldilocks!

**Summary for the Chapter:**

> Goldilocks gives Quinn an interview!

Adam “Goldilocks” Bradford-Texarkana meticulously eyed Quinn as he rambled on about his boring life and intentions of wanting to attend the auction. He analyzed every part of Quinn, from his alluring slight southern drawl (which the boy tried but failed miserably at concealing) to his, admittedly, nicely chosen sissy clothes.

Goldi didn’t like what he saw.

Not because Quinn was ugly. Quite the opposite.

When Goldi walked in, expecting to meet some cheaply dressed, ugo, sissy wannabe, but instead he found a gorgeous caramel skinned hottie sitting in his living room, he was stunned. This boy was insanely cute in person!

This boy could pose a threat to him, and he was quickly starting to regret giving him an interview.

When he first saw that someone had messaged him on SissyBoy.net, he was gonna ignore it. It was probably some beggar wanting something from him or his daddy, but still he read it anyways.

And he was right.

It was just some lame-o who wanted a spot in one of the biggest sissy events of the year at his daddy’s club.

Pathetic.

But what piqued Goldi’s interest in this particular message was the fact that he didn’t recognize Quinn’s name, and he knew all the sissyboys in the area (ALL of them).

Who was this boy? Where did he come from?

He glanced through his profile to learn that…..

Nope. He still didn’t recognize him.

He didn’t see him at his school, so he must have gone to public school and obviously didn’t come from wealth. He was a cute boy, and he saw that he had a decent sized following. Nothing compared to the 900,000 people that followed him, but he saw that he had potential.

_How curious._ Goldi pondered. 

Now he couldn’t just ignore it. He had to know who this new sissy was. Plus, the message was dripping deliciously with desperation. Goldi did consider himself quite the good Samaritan, so he couldn’t just say no.

_Eh, what’s a little more competition._ He thought.

He was sure that he was gonna win the pageant and get the most bids anyways. He always did. Ever since he first entered the pageant three years ago, before he married daddy two years ago, and even now that he was married, he still won the top bids, and the lucky winner got to spend one heavenly night with him, the “Golden-haired sweetheart” of East Texas. The opportunity of a lifetime.

He had absolutely nothing to worry about.

So, he agreed to meet up with the boy that Friday.

That Friday afternoon Goldi planned on meeting him, he was gonna skip his last period class, but his stupid math teacher threatened to call the truancy officer if he skipped again.

Excuse me??

This bozo new teacher of his was really getting on his nerves! Always pestering him to do ALL his work, making him attend class every day or else he’d fail him. He even commented on how inappropriate his uniform was. That day, he threatened Goldi that if he didn’t change his uniform, he was gonna give him detention.

Oh, that tears it!

His schoolwork was one thing, but NO ONE tells Adam ‘Goldilocks’ Bradford-Texarkana what he can and can’t wear! This fool didn’t understand that he could do whatever he wanted because he was RICH! Both of his daddies shat out every morning more money than what this clown teacher made in a whole year’s salary! It was time for him to put an end to this teacher’s nonsense.

“Is everything all right, Adam?” Principal Matthews asked when Goldilocks burst into his office, visibly distressed.

“I don’t know, sir.” He swooned against the principal’s desk. “It seems that the new math teacher, Mr. Tanner, doesn’t like me or something because he keeps threatening me with detention and failing me, unlike all my other teachers. He just doesn’t understand that I’m trying my very very best! Still, he can be so unrelenting! He even commented on my uniform! Even though I wear the same uniform as everyone else! If he keeps harassing me like this, I just won’t know what to do!” Goldi let a single crystal tear fall from his sapphire eyes.

“How horrible!” Principal Matthews stood from his desk in a rage. “I’ll make sure to fire him immediately for giving you such a hard time!”

“No no pleease don’t do that!” Goldi begged, rushing around the principal’s desk to clutch his arm. “I’m sure Mr. Tanner’s a good man, who needs to keep his job to provide for his family. He just doesn’t understand that I’m trying my very best. Please, just _make_ him understand like all the other teachers. Will you do that for me, pleease?”

The principal was tearfully moved by the boy’s generosity. “Even when you’re being personally wronged, you’re still such a considerate angel of other people!” He relaxed back into his chair. “Very well. I’ll talk to him and make sure he is more lenient with your grades or there will be consequences.”

“And what about my uniform?” Goldi leaned against the desk, spreading himself out in front of the man. “You like my uniform, don’t you Principal Matthews?”

The principal swallowed as his eyes molested the boy’s erotic body. “Of course. All the teachers here do.”

“Mr. Tanner doesn’t.” Goldi pouted and spread his legs more.

“D-don’t you worry.” His eyes were glued to expanding bulge in the front of his tight shorts. “By tomorrow, there will be no more nonsense from him about your uniform!”

“Oh, thank you Principal Matthews! You’re such a kind caring man!” Goldi threw his arms around the man and hugged him tightly. “I’ll make sure my daddy knows what a fine job you’re doing here. He’ll reward you greatly.”

He traced his finger up the man’s chest and tugged playfully at his tie.

“And please let me thank you as well.” Goldi purred in the man’s ear.

He didn’t object as Goldi crawled on his lap and pressed his soft lips against his, the boy’s sneaky tongue slithering into the man’s mouth.

The principal was a young guy, well, younger than Goldi’s husband, and he was always eager to comfort Goldi whenever he needed it.

“Are you sure Mr. Texarkana won’t have an issue with this?” The man always hesitated, but his hard cock was pounding at the front of his zipper for release.

Why should he care? He was sure daddy had other boys on the side, so why couldn’t he play around too.

“You’re the only one who can comfort me right now.” Goldi said, rubbing himself across the man’s erection, and guiding his hands around behind him so he could squeeze the boy’s ample ass. His naughty fingers deftly undid the man’s belt and pants then teased his hot thickened rod and played with his hairy balls.

Principal Matthews lost all decency as an educational administrator when it came to Goldi. All he cared about was sinking his cock deep into the boy’s tight milky ass. He threw Goldi onto his desk then tore open his unregulated uniform shirt and kissed and sucked on his pretty pink nipples.

His skin was so hot and soft that he thought it would melt through his hands. He quickly went to his knees and pulled Goldi’s stiff cock from his little shorts. It was as smooth and porcelain as the rest of his body, but its mushroom tip was a tempting scorching red.

“No Principal Matthews! I’m supposed to be rewarding you!” Said Goldi.

“Getting to taste you is a reward.”

The man sucked his sissy cock into his mouth, and Goldi gave an irresistible shiver. Principal Matthews engulfed him all the way to the base, and his tongue flicked the sensitive spot underneath the head of his cock, making Goldi squeal and writhe in pleasure.

“Hurry Principal Matthews, fuck me! Fuck me! I want your cock!”

Of course, the man couldn’t resist him when he begged like that! He flipped the boy over on his stomach, pulling his shorts all the way down and slid his aching dick into the boy’s ready hole.

He thrusted like a madman as he buried himself balls deep into the boy’s snatch and enjoyed the view of his large fiery handprints on his porcelain rump as he pelted out spankings onto it. He never got tired of fucking Goldi’s tight ass. Too bad the boy was a senior, and he probably won’t get to fuck another sissy for a while.

His balls churned as he fucked Goldi furiously, and the moaning beauty kept crying out for the man to fuck his boyhole harder, faster, deeper, and how he wanted the man’s melty cum inside of him right now.

With an undignified roar, he gave Goldi what he asked for. In his earth-quaking orgasm, he filled the boy with his man milk while thanking God for giving him the best job in the world.

Eventually the principal reluctantly let the boy go and collapsed back into his chair.

Satisfied for now, Goldi straightened up and fixed his clothes.

“Thank you, Principal Matthews. You always take such good care of me.” Goldi praised the man with big dreamy eyes.

“If you need-” He exhaled in exhaustion, “Anything else, please let me know.”

“Sure.” Goldi walked out of the office, leaving the man a sweaty disgraceful mess.

Done and done.

Now that that idiot teacher was out of the way, it was time to go meet what’s his name— Quan.

But first he needed a chai iced latte to refresh himself.

He hopped in his sports car and zoomed down the highway towards his favorite upscale café. He veered to the right to take the exit, cutting off a couple of cars and an 18-wheeler that was in his way, prompting a motorcycle cop to pull him over. 

Who the hell was this dope?

All the cops knew his car and knew better than to menace him.

“Did I do something wrong, Officer?” He batted his pretty golden lashes at the cop while simultaneously catching the man’s name and badge number so he could report to his daddy about the idiot cop who decided to pull him over.

“Nothing terrible. You just cut across three lanes without a blinker, almost made an 18-wheeler crash, and you ran over a few traffic cones at a construction site. I just pulled you over to tell you to drive more carefully. I wouldn’t want anything bad to happen to you, Mrs. Goldilocks Texarkana.” The officer grinned through his aviators.

Oh, so the cop did know who he was, and judging from the man’s grin, he had more things in mind than just giving him a citation.

“Oh, Officer Caldwell, you know who I am?”

“Why I sure do! You’re my favorite idol. I was a huge fan of your “Goldilocks and the Three Bears” video you did two years ago. It really uh— blew my mind.” His grin grew even more sleazy.

Goldi feigned surprise. “Oh, it’s always an honor to meet one of my many fans! And thank you for your concern, Officer! I’ll be sure to drive more careful from now on, and I’ll make sure to tell my daddy what a fine officer of the law you are.”

“Thank you very kindly, but I’m afraid that since you were swerving on the road quite a bit, I’m gonna have to ask you to step out of the car, so I can pat you down for any controlled substances.”

Goldi decided to play along. Even though he was just a lowly civil servant, it was always good to have a few cops in his tight back pocket. Plus, something about men in uniforms did get Goldi’s sissy cock all tingly.

“Of course, Officer! One must do their job thoroughly.”

Goldi stepped out, put his hands on the hood of his car, and spread his legs wide, jutting his ass out for the officer. Officer Caldwell stepped behind him and began patting him down, starting from his tight calves, up his delicate knees, then his fingers crept between his soft thighs, grazing against his crotch, and Goldi gave him a little moan.

“My, you sure are wet down here.” He felt between Goldi’s ass cheeks. “Perhaps it’s drug paraphernalia?”

“You’re welcome to search further, Officer.” Goldi grinned.

That he did.

The officer pulled down Goldi’s shorts and inspected his drippy used boyhole with two eager fingers, reaching deep to press against Goldi’s sweet spot, making him shiver and moan for the officer’s cock. Then he pressed Goldi against the hood of the car and fucked him in front of the passing cars on the highway. He fucked Goldi as if he had been waiting two years to do so, and the four hot blasts that erupted and overflowed from his asshole could prove that idea.

“Make sure to drive safe now.” The officer said once he finished up. “If you need the police for anything, you make sure to call me first, ok?”

“I will, Officer, and I’ll tell my daddy what a reliable policeman you are! Ciao!” Goldi got back into his car and sped off again.

Now he was more than 45 minutes late for his interview with Quincy, but now he was thirsty for his chai latte more than EVER. So, he went to his favorite café and got out to order his drink inside. He preferred to get out and order at the counter.

“Here for your regular, Mrs. Texarkana?” Derek the barista smiled at him.

“Duh.” He turned his nose up at the servant, but Goldi felt his face flush. Derek only laughed in response.

“Alright. Iced chai latte with fat-free milk, comin’ up!”

Goldi watched Derek the barista make his drink. To him, he was the only person in that café that made a decent latte.

There was something about Derek the barista that intrigued Goldi. This guy was the first person to ever call him out on his ingenuine façade, commenting that “there was more to your good boy front than what meets the eye.”

That insolent comment triggered Goldi’s hate yet slight admiration for Derek the barista.

Slight.

He was a 21-year-old community college part-timer with long brown hair, a scruffy beard, and a body covered in piercings and ridiculously crude tattoos. How he got the job at this upscale café was a true cause for concern. He looked like a dirty hippy. He was a peasant really. The complete opposite of his clean-cut daddy.

Even though Goldi would NEVER in a million years think to have a boyfriend or husband like that, he often came in to see him and couldn’t help but to flirt with the guy. It made Goldi feel naughty to be flirting with someone so beneath him! Plus, under his dirty hippy beard, he had a nice smile, and he could also see underneath his dirty ripped jeans, the outline of a nice fat cock that made Goldi’s mouth water.

“How’s the sissy life treating you?” Derek asked sincerely.

“Obviously great.” Goldi huffed then grinned impishly. “You should try it with me sometime.”

The older guy laughed. “Thanks for the offer, but I can’t. It’s not really my thing, and I have a girlfriend.”

He made another noise with his mouth. “You and everyone else, but whatever.” He snatched his drink from him. Then for the first time, Goldi did something outrageous. Something he would have never done for such a simple half-educated nobody like Derek.

“Whenever you change your mind and feel like trying out a top notch sissyboy, shoot me a message.” He slid Derek the barista his SissyBoy.net profile card. “You may find out that I can do many things a lot better than your boring girlfriend ever could.” He gave Derek the barista a suggestive lick of his lips then left.

He’d give in. They always do.

Finally, Goldi was able to make it home without another issue. He was ready to meet this person, and be finished with his busy day, but now he had something else to worry about.

He had underestimated Quinn. He had seen many cute sissies before, but there was something about this boy that made him feel threatened.

But why??

There was nothing truly special about him!

Maybe.

Besides the fact that he was gorgeous.

Any sissy wannabe could slap on a pair of panties and post a picture and be cute, but what made a sissy an idol was having the perfect niche, and he believed that once this boy found his, he would be dangerous to his place in the top 5, so it was time to really scope out the competition.

Quinn was still rambling on when Goldi stopped him. “Alright, alright. I’ll talk to my daddy about letting you in, but first you have to do something for me.”

Quinn had to stop himself from jumping up and kissing the boy!

“Thank you! Thank you! Of course! I’ll do anything!”

“Good.” Goldi grinned. “I have to test and see if you’re quality goods. No daddy’s gonna want a boy who can’t satisfy him. So I’ll be the one to test you out. If you pass the test, I’ll grant you a spot in the pageant.”

“Ok.” Quinn hesitated, but had a feeling that he knew where things were headed. “What’s the test?”

He didn’t want to, but he was determined to get a spot in the pageant no matter what!

Still, he was apprehensive of losing his cherry to Goldilocks.

Goldilocks read the apprehension on Quinn’s face. He didn’t have to worry. He wasn’t gonna fuck him, but he was gonna test him out in other ways.

He stood in front of Quinn then told him to get to his knees.

“Show me what that mouth can do.” Goldi grinned sadistically.

The newbie did have some rather plump looking lips that he was eager to try out.

Quinn wasn’t new to blow jobs. Thanks to his father forcing him to go to summer camp when he was 15, where he and an old redneck friend of his spent quite a bit of alone time together (Thus, making his camp experience a rather enjoyable one), he was pretty skilled at them. Also, thanks to practicing on toys.

He got to his knees, and Goldi’s hard boy peen bobbed out as he released it from his little shorts. His tip smelled a little sweaty, and it was a naughty red color and hairless. He slowly teased the head of Goldi’s cock with his tongue then used his perfect lips to slide down the shaft, making the other boy gasp and his knees buckle. He eased more of his cock into his throat then started steadily slurping on it.

Quinn wasn’t hating this. In fact, he stuck his hand down the front of his own shorts and played with his own hard sissy peen. The subtle tangy flavor of Goldi’s precum was turning him on, and Quinn was getting more into it as he listened to Goldi moan and felt him tugging on the top of his hair.

“Oh my god…oh my god….” Goldi mewed and bucked his hips into Quinn’s face.

_Holy shit, this boy is skilled!_ He thought as Quinn licked his balls then engulfed his cock head into his mouth while moaning on it.

He doesn’t suck like someone who hasn’t done this before, and he looked incredibly hot underneath him. This boy was gonna make him cum super quick!

He pushed his head away. “Let’s move on to the next test. Strip now.”

Quinn stripped off all his clothes, so that Goldi could have a look at him.

He had a nice, feline, caramel colored body. He must have been a ‘mixed breed’.

Everybody loved those!

That was something else he had to consider.

Goldi stripped from his clothes too then made Quinn lie back on the pool chair. He got on top of him and Quinn couldn’t help but hump his cock between Goldi’s soft wet butt cheeks.

Goldi was enjoying the feeling too as he rubbed his hand across Quinn’s smooth torso and teased his cock between his cheeks. It had been a while since he had sex with another sissy.

“This isn’t part of the test.” Goldi said then flipped around and bent over so that Quinn was face to face with his smoothily waxed, bleached, but obviously freshly used butthole. “Make sure to do your best.”

This was gross.

Quinn didn’t want to lick Goldi’s used hole, but he had no choice. He’d lick a thousand used assholes if it meant he would get a daddy!

Maybe.

He stretched his tongue and slowly rimmed the wet puffy opening. It was so sopping wet and gaping, he could see Goldi’s pink insides. Goldi rolled his hips to match Quinn’s tongue strokes. The erotic look of the other boy’s hole and acrid taste made Quinn grab Goldi’s thighs closer, so he could plunge his tongue in deeper into his sissyhole.

Goldi cried out and thrusted his ass back on Quinn’s tongue.

“Yeah, keep tongue fucking me!” Goldi cried out against his own will. It felt too good to not want more!

This was bad! Really bad!

Quinn’s hard cock was in his face, so he sucked it into his mouth making Quinn immediately respond with a spurt of precum.

He’s so responsive and moaned like a sexy sissyboy! This was another problem!

Quinn writhed and groaned as Goldi hungrily sucked on his hairless sissyboy cock and massaged his pretty balls. Goldi spread his cheeks to get a peek at Quinn’s hairless boyhole.

It was still tight and virginal! Oh, this was a BIG problem! Virgin sissies were rare and valuable. HE even was turned on by it and had to give it a few licks.

The boys were so loud and wild in their 69ing that it got the attention of Goldi’s servants who made sure not to interrupt the two fully naked sexy boys.

Even though Goldilocks was a spoiled little bitch, it was still hot to see him doing naughty things. They all watched from behind the backdoor, hands in the front of their pants, as the two sissies groaned like sluts and humped each other’s faces.

They would have to tell Mr. Texarkana about this. They knew he would be angry at the fact that he wasn’t there to see the two sissies messing around in his own house then they would have another pleasure of hearing Goldi’s sexy cries through the walls that night when Mr. Texarkana would come home and punish the naughty boy.

Quinn used two fingers to repeatedly press the small hard lump in Goldi’s ass which made his balls tighten up, and he clenched around Quinn’s fingers before hollering and firing off creamy ropes of jizz all over Quinn’s stomach. He pressed and pressed until Goldi’s milky streams ceased fire, and he cried out from oversensitivity.

Goldi’s head was all swimmy from his powerful orgasm. He had to roll off Quinn and lay still for a minute.

His sissy instincts were right about this boy! He couldn’t let Quinn in the pageant. He would ruin his winning streak if he did, so he had to stop him no matter what.

No.

He had to absolutely crush him.

Humiliate him.

Break his spirit completely, so he wouldn’t be a problem to him in the future.

“Congratulations Quinn.” He sat up and smiled at the boy. “You’ve passed the test. I’ll make certain you have a spot in the pageant.”

Quinn was so happy that he didn’t even care about his still throbbing erection, and his abdomen was painted with jizz.

“Oh my god! Thank you so much, Goldilocks!” He squealed. “I’ll never forget this!”

**Notes for the Chapter:**

> Dudes..I made the hilarious mistake of running "SissyBoy Sagas" through a text-to-speech narrator program. DON'T DO IT!
> 
> Lmaoo
> 
> But if you do decide to do it, please let me know if you prefer to read it or listen to it! Warning: it sounds crazy weird!


	4. Quinn Meets his New Daddy!

**Summary for the Chapter:**

> It's the night of the pageant. And Quinn arrives with high hopes to meet his dream daddy and lose his virginity!

Tonight was the night that would change Quinn’s life forever.

Close to midnight, he took a taxi to the exclusive private country club an hour away from his house and almost 1 mile away from the main highway.

The club’s huge iron gates were open and receiving the fancy expensive cars of all the patrons pulling into it.

It was a little embarrassing for him to arrive in a disgusting yellow taxi while everyone else poured out of stretch limos and sleek luxurious cars, but nothing to worry about! At the end of the night, he would be leaving in one of those fancy cars in the arms of his new rich man-candy!

The anticipation of the night ahead had him squealing in excitement. He was gonna lose his virginity tonight! That’s what excited him most of all! He was gonna finally feel a man deep inside him. Taste a real man! Be made manly love to by a sophisticated handsome man! He was finally gonna have his fairytale first time!

His taxi pulled into the club’s gates, and he stepped out at the entrance in his all-pink ensemble. He spent all his savings on this outfit. Going for the Beverly Hills wife look (in hopes to attract a Beverly Hills type of man), he was pretty in pink with his hot pink choker, skin tight yet off-the-shoulder crop top and tight hot pink shorts, along with a pair of sheer thigh highs, and a new pair of pink velvet platform heels.

He looked hot as hell!

But he was the only one in pink.

In any colors.

All the patrons in their black and white suits were staring at him like he was crazy.

W-what was going on?

Goldi told him the event was informal.

It’s ok. Once he was inside, maybe he could borrow a suit from a fellow sissy.

No big deal.

With his head held high, he approached the concierge at the wide double doors.

“Pardon me,” Quinn said. “My name is Quintan Kubiack. I’m a contestant in the pageant.”

The man’s eyes barely glimpsed at the paper in his hand.

“There’s no one by that name on the list.”

“What? Well, check again. I’m supposed to be here.”

“Well, you still ain’t on here. Now you gotta go, pinky.” He shoved Quinn out of the way to let other people in.

“Huh? There has to be a mistake!” Quinn started to panic. “I was personally invited by Goldilocks. Adam Texarkana!” I went to his house! He said he would get me in!”

“I didn’t get that memo, so you’re shit outta luck. Beat it.”

Quinn was sick to his stomach. The world around him was starting to spin out of control. Everyone was staring at him. Laughing at him!

He turned around and saw Goldi step out of a limo in an all-white tuxedo jumper with his entourage of sissies trailing behind him.

Oh, thank Christ! He could just go in with Goldi!

“Hey Goldi!” Quinn ran to the boy but was intercepted by one of the security guards. “Hey! Hey! Lemme go! The man said I ain’t on the list, Goldi. What’s goin’ on?”

“The man said I ain’t on the list, Goldi!” One of Goldi’s posse mocked Quinn in an over exaggerated country accent. “Were you raised by farm animals in a barn?”

They laughed at him.

Goldi laughed at him.

Everyone laughed at him.

His world was now starting to cave in around him, and he tried to keep his voice from shaking.

“G-goldi, you said you were gonna get me in!”

“It’s a sissy eat sissy world!” Goldi sneered at him. “Try again next year, wannabe!”

They all howled in his face.

But suddenly, that quick right hook that Quinn’s father taught him how to throw when he was 8, instinctively came flying out and popped Goldi in his right eye.

The blonde yelped and stumbled back. His eye was already swelling shut, purplish and ugly.

Good!

He was blinded with fury!

Quinn managed to let his fists fly and pop angry shiners on more of Goldi’s entourage too. But as he was getting ready to snatch Goldi by the hair, three security guards came and pried him away from the group and held him back like a rabid animal as they ushered Goldi safely inside.

“You bitch! I licked your sloppy asshole for this!” Quinn shouted as the guards carried him away. “This ain’t over!”

Quinn was numb. His mind, blank. He didn’t even fight back when the security guards drove him in a golf cart to the gate then shut it in his face.

He didn’t call a cab. He mindlessly staggered down that dark mile towards the highway truck stop station, ignoring the cars honking and shouting obscenities at him. He had sweat off his mascara, and his pretty clothes were ruined. One of his nails was painfully cracked from punching Goldi in the face, and he tripped and fell on the uneven ground, snapping off his right high heel, causing him to limp the rest of the way.

Quinn made it to the bleak truck stop and went into the stinky men’s restroom. There, he limped into the very last stall then sat on the toilet seat.

Then the hot tears spilled from his eyes and rained down his rouged cheeks. He curled up on the seat and sobbed loudly.

This was beyond the worst day of his life! He had been utterly embarrassed!

That was his one chance to skyrocket into fame, wealth, marriage, and become a top idol sissy!

He uselessly tried to swipe away the torrent of tears from his eyes.

Now, word of his disgraceful scene at the club would spread all over the forums on SissyBoy.net. Either he would be in jail for assaulting Goldi! He was gonna be the laughingstock of the whole web when they found out about him! He just wanted to die!

In his loud sobbing, Quinn didn’t hear the restroom door open or hear the bootsteps coming towards his stall.

His stall door flew open, startling Quinn, and a huge bearded man appeared in the doorway.

The big man who opened it was obviously a trucker, his dirty work boots, jeans, and gray T-shirt, and cap that read ‘Trucker’ indicating that as well.

He looked like a giant grizzly bear with his thick brown beard, straggly hair covering his arms, and bushy unkempt hair spilling out from his cap. His bulky lumbering body, the complete opposite of Quinn’s schoolboy frame, blocked the entire doorway, prohibiting Quinn’s escape.

“Who are you? Go away!” Quinn snapped.

“You the new cumdump?” the stranger’s disorientatingly baritone voice and heavy East Texas accent asked.

“The what?”

“Look where you at.” 

Quinn had no idea what the hell the man was talking about, but he looked around the stall and noticed that there were glory holes in the stall’s left wall, and used condoms littered the floor. Phone numbers scribbled across the walls that offered “hot nights” and “cock sucking heaven call here” were everywhere.

Oh my.

OH MY!

“E-excuse me!” Quinn stammered. “I ain’t a truck stop whore!”

The man looked unconvinced. “Then why you in here?”

“A mistake!”

Did this man really just mistake him for a cum dumpster? Unbelievable! This night couldn’t get any worse!

But….the quick idea of it, did cause a weird surge through Quinn’s body, down to his cock.

“Lookie here, boy. I came all the way here to get some ass. This my last night in town for the next two weeks, and someone’s gettin’ fucked tonight,” the bear man undid his belt and pants, approaching Quinn menacingly. His monstrous hard cock sprang out the opening, shaking Quinn to the core.

“W-wait!” Quinn held out his hands to stop him. “I ain’t some truck stop cumtoilet! I am a top dollar sissyboy!”

“A what?”

“A sissyboy!” Quinn put some resolve back in his voice. “A beautiful, princess, delicate, masterpiece that graces only few people, and I DO NOT FUCK in a dirty stall! And another thing—”

He paused.

Maybe he was just desperate to lose his virginity before his birthday. Afterall, he did think he was going to lose his virginity that night! Dammit, he wanted a man so bad! He was so close to tasting his fantasy man, it drove him crazy!

Perhaps he had truly hit rock bottom, but he was ACTUALLY considering the trucker’s offer, and especially becoming aroused by the depravity of the situation!

Ugh!

What the hell was wrong with him??

Even though he was a complete stranger, this beefy guy wasn’t so ugly. He sorta reminded him of his daddy.

But thankfully, the man had stopped moving towards him.

Quinn cleared his throat, wiping away his remaining tears and the snot running down his nose.

“It just so happens that I am in the market for a daddy. So, if you buy me something nice to wear, and with a change of location,” he gestured to his dirty surroundings, “I’ll let you indulge in the flavor of the sweetest sissyboy you will have ever tasted.”

“I got $300 and the back of my truck,” the man stated.

Quintan thought.

“Very well, bear man,” he got up and followed the man out of the restroom.

Yep, this was it.

Quinn had truly hit rock bottom.

Whoring himself out for an hour to some disgusting trucker for chump change! He was pathetic! For all he knew, this man could be leading him to his truck to murder him and do vile things to his dead sissy body!

If that happened, at least he wouldn’t have to face the embarrassment and shame of the humiliating comments of the sissies on SissyBoy.net the next day.

The man’s truck was a big blue 18-wheeler. Quinn thought the dude was gonna open the back doors and throw him in and carry him off to his twisted death, but instead the man opened the truck’s passenger side door and behind it was a little room that contained a modern comfy looking bed, a small flat screen tv, a microwave, and a table.

Not what he was expecting.

The interior seemed rather luxurious for a truck.

Quinn was more intrigued than fearful as he climbed in and sat on the somewhat soft bed then the man sat next to him. Quinn wanted to ask what he should do next, but the man answered by undoing his belt and zipper again, and his hard cock sprung out. It was great and angry looking.

“Suck it first before I stick it in your ass,” he said.

This brute!

Disgusted but in too deep now to quit, Quinn knelt on the floor in front of him. He took the stranger’s stiff cock in his hand. It felt so hot and rigid in his palm. A thick, heavy, man cock he had never felt before! Its reddish swollen head was leaking obscene man juice, and the sweaty, musty smell of the man’s dick filled the small cab and made Quinn give a little hungry moan.

A real man’s cock! Even if it did belong to a dirty trucker, it was so beautiful. The base of his cock was shrouded in a bush of dark pubes, but Quinn could see the man’s large round balls underneath.

Quinn wrapped his lips, made for sucking dick, around the man’s dickhead, and the man sucked in air as Quinn went further and further down on it.

“Damn, that’s nice!”

The man’s cock left a strong almost onion taste in his mouth, but Quinn kept sucking his first man cock, savoring the taste of it!

“Yeah suck it, you slut,” he said while moving Quinn’s head back and forth. He couldn’t fit all his girthy cock in his mouth that he was trying to push down his throat.

The man reached down and pulled the back of Quinn’s shorts down, revealing his new lacy white G-string he had bought for this supposed to be special night.

The man snapped the string of Quinn’s panties and yanked the string harder between his ass cheeks.

“You like wearin’ panties and stuff?”

“Duh,” Quinn answered.

“Ain’t the first time I seen that,” he kept massaging Quinn’s soft ass cheek with one hand as his other yanked the string harder.

This inconsiderate monster was ruining his nice panties! Yet Quinn’s cock could barely be contained in the sheer fabric.

Quinn sucked harder on his cock, moaning on it, making the man grunt every second like he was getting closer and closer to orgasm.

“Hold up now,” the man reluctantly pulled the sissy’s hungry lips off his cock. “I wanna stick it in before I cum all over the place. Them lil’ queer lips of yours ain’t no joke.”

_The first smartest thing the man said all night_, Quinn thought.

Quinn stopped and fixed his hair.

“Since my sweet boyhole is still virginal and fresh, you can only use luxury condoms and lubricants. Do you have any Ruby Rubbers?”

The man reached into a drawer and pulled out a box of condoms. “I got magnums.”

Quinn rolled his eyes.

“At least do you have any Diamondhole Lubricant? Richboy Jelly? Or Slickysissy Lube?”

“I got spit and Vaseline,” he reached into another drawer and pulled out a huge jar. “Take your pick.”

This cretin!

“Ugh! Fine. Give it here.”

Quinn snatched the jar and got on his knees on the bed. He applied the greasy stuff to his hole. He really couldn’t believe he was doing this! And he was still considerately hard!

What an immoral slut he was!

Then the man slid on the condom then scooped out some Vaseline from the jar like he was scooping the guts out of a Halloween pumpkin then smeared the wad of it all over his dick.

“Damn you got a sexy ass, boy.” His rough hands squeezed Quinn’s soft bottom.

_Second smartest thing the man said all night._

The man spread Quinn’s cheeks apart, exposing his hole. Quinn was about to tell the man the proper way of how he was supposed to make love to his princess hole, but the bear man’s greasy penis popped into Quinn’s hole before he could get a word out, and he was stunned with pain. When he opened his mouth to scream, the man pushed more inches in, snatching his breath away.

“Ah shit!” the man grunted. “The tightest cunt I ever did felt!”

Quinn gripped the sheets. His whole body felt fevered from the hot pain flaring from his hole being stretched.

Getting fucked in the ass hurt!

He pushed in inch after thick inch that Quinn thought was never going to end, but finally he felt the base of the man’s cock resting against his ass.

“You ain’t took no kinda dick before?”

“Toys,” was the only word Quinn could breathe out.

The man adjusted his position once he was all in then started thrusting and Quinn whined with each thrust.

His dick was well lubed up, but that didn’t make the pain of his virginal hole being pried open any less painful!

His greasy dick slid in and out smoothly and steadily, making lewd macaroni and cheese noises in the small cab.

Then he dug his calloused fingers into Quinn’s soft hips and pistoned while calling him a ‘little slut’, a ‘nasty bitch’, or his hole a ‘tight boyclam’, all indecent things he never imagined the man of his dreams would call him! Quinn couldn’t believe he was losing his cherry to such a dirty, grunting beast.

And it was fucking hot!

He kinda liked this man talking dirty to him, calling him names, smacking his ass, getting fucked like an animal!

The man’s unfairly massive body size kept Quinn pinned in place from moving anywhere as he fucked him, never taking his length from Quinn’s hot sissy tunnel. The pain slowly melted into a deep filthy pleasure, stiffening his sissycock and making it bob up and down underneath him with each ram of the man’s hips.

His face was buried in the cologne smelling blankets, his eyes watering from the prying feeling in his hole, and the way the man’s dick was reaching so unbearably deep. Past the point of his toys or fingers could ever reach.

“That feels good!” Quinn groaned out loud, and the man took that as his cue to start jackhammering the boy into the mattress, and Quinn screamed.

The truck rocked as the bear man’s cock ravaged Quinn’s guts, elevating him to higher heights, and making him moan and beg uninhibited like the proper sissyboy slut he was.

“Please don’t stop! Please don’t stop!” he begged.

“You like gettin’ your stuck-up pussy fucked, huh?”

“Yes sir! Fuck me more, you disgusting man!” he didn’t want this feeling to end, but he had to stroke his cock to messy completion, spurting his sissy cream across the man’s mattress.

“Fuck this, I’m cummin!” the man thrusted in a barrage as Quinn’s orgasming hole constricted around his cock, making Quinn lose his balance on the bed.

The man rocked Quinn as he came once- twice- a third- oh a fourth? No, a fifth time, until he shivered a last final time then loosened his grip on Quinn who was covered in sweat, his back covered in the man’s sweat, and his head in a haze. He felt like he had literally been fucked stupid.

The man let go of Quinn, tossed the sticky fully loaded condom into the trash, then went to the front seat to sit.

“That was incredible,” Quinn sat up awkwardly and fixed his clothes.

“Your ass was somethin else too,” The man smoked on a post-coital cigarette. “You wanna coffee?”

“I want my money.”

The man reached into his wallet and gave Quinn three bills.

Quinn took the bills, but the shame of the night’s events came flooding back to him.

“This wasn’t supposed to happen!” Quinn tried to not start crying again. “I’m supposed to be with a rich, handsome man from the country club! Not getting fucked by a filthy redneck rig driver! No offense.”

The man puffed on his cigarette.

“Still,” Quinn sighed and leaned against the seat. His ass, an empty wanting vessel for more of the man’s dick. “Your cock was amazing.”

“Been told that before.”

“What’s your name, bear man?”

“Maxwell.”

Quinn didn’t like that. Daddy Maxwell didn’t roll off his tongue very well.

“Like I said earlier, I am on the hunt for a daddy.”

“Already got two kids. Don’t need another.”

“Not that kind of daddy! You buy me things and do as I say.”

“You a runaway or somethin?”

“No! Just a sissy a little down on his luck,” Quinn didn’t want to admit.

He couldn’t go back home without a daddy. Before he left, he had bragged to his confused daddy that he wouldn’t see him without his new husband from now on! He was too embarrassed to go home without one!

“Oh, like a sugar daddy or somethin,” he finished his cigarette and flicked the butt out the window. “Don’t know if you’re a runaway, but long time ago, I used to have me a little queer boy like you that wore dresses and stuff. Didn’t know your type had a name though. Up and ran off on me. Miss his lil’ girly ass too. Could use another. So, I tell you what, I’ma good Christian man, and I got a house 10 minutes south of here. Out in the country. I’m gone for weeks at a time sometimes. Driving a rig and such. You go out there and clean up and feed my dogs, I’ll be your daddy.”

Quinn clutched the pink choker around his neck.

Clean?

Feed animals??

Working???

That’s not having a daddy, that’s slavery! He couldn’t do that to him. Quinn had civil rights!

But the man said he’d be his daddy. Someone offered to be his daddy!

“You’ll buy me pretty things and give me money?”

“Once I see you ain’t burnt my house down.”

Quinn was giddy! His own daddy!

Perhaps Quinn was going about things all wrong all along. Maybe he needed a not-so-rich daddy first then level up to a richer one later. So, he decided he’ll stick around with this trucker until he found a better one in the future. Keep on the lookout.

Even if he was a filthy redneck rig driver, the man did just blow his back out then fork him over $300! No online shopping in the clearance section tonight!

Quinn was tired of taking ugly taxis everywhere he had to go! But he had to take another one to the address the man told him to go.

When he woke up that next morning, he felt refreshed rather than shamefaced for having sex with a stranger at a truck stop.

He had finally had sex! Even though he was still aching a little from it, it was soo fun!

He wanted to do it again. Badly. He was ready to feel that redneck’s horse cock inside him again.

The taxi took him out to the address, and Quinn was still a little apprehensive, thinking the man was still trying to send him to his brutal murder. He didn’t know what to expect!

But when he arrived at a small rural neighborhood with nice brick houses all over the place, he was pleasantly surprised. He was stunned to find luxury log cabin like houses with pools in their backyards and acres of plush land everywhere. Like something out of Southern Living magazine!

He saw the man’s blue semi parked on the street in front of the man’s house.

A nice house.

A big one. A two story, redwood, luxurious cabin house!

The neighbors gawked at Quinn in strange bepuzzlement, wondering who this boy was stepping out of the taxi in his tiny red biker shorts and yellow crop top that read “Sissy” on the front.

Maxwell was waiting for him in front of the house.

“Dude, your house is huge!” Quinn couldn’t take his eyes off it.

They went inside and the interior was spacious and nice, but the furniture and décor weren’t great, considering the man’s redneck tastes. But don’t worry, since Quinn would be living here now, he would have it fixed up immediately to his liking!

“How do you have such a big house from just driving trucks?”

“I own a truckin company,” he answered. “Rent out services outta about 10 trucks. I make a good penny.”

“You own a company yet you’re driving the trucks? Why?”

“I like drivin trucks.”

“That’s such a lowly job!”

“Money can’t buy happiness.”

Just when Quinn was giving the man the benefit of the doubt, he went and said another stupid thing.

Of course, money buys happiness!

“Just how much do you make??”

“Don’t ask a man about his money,” the man opened the front door and gave Quinn a ring of keys. “Now, I’m gettin ready to go. Take care of my house, boy and I’ll give you a little allowance. You up and hightail it outta here and stuff come up missin, don’t think I can’t hunt you down, ya hear? This here is one of my houses in the city. Keep it clean and go down to the other one down the street and straighten it up too. I’m countin on you cause I can’t trust my goddamn sons to do nothin. They always fuck shit up.”

Sorry, what???

Did he say ONE of his houses???

“How many houses do you have?”

“Just two. But I used to build houses and now I rent out about 10 in the city and 10 outside of it.”

What was even happening??

Oh, he was definitely gonna stick with this man for now! All of this lucrative news he was learning about his new daddy made Quinn fall to his knees in front of said daddy and take his cock into his mouth.

He gratefully sucked his cock, getting it nice and hard in front of all the passing neighbors, walking their dogs or watering their grasses. The man postponed his leave by a couple of hours to aggressively break in his new sissy in the doorway, on the couch, and in the bedroom, making sure that Quinn was well acquainted with the new kind of sex that he would be having from then on. Which Quinn was quickly learning that he loved, and as long as he kept giving him money and serving him that fat dick, he’ll stick around for a long time!

“Our story was almost like a Cinderella story, or Beauty and the Beast (whatever),” Quinn bragged on his SissyBoy.net profile page. “It was the night of the Ball. My outfit was stunning. Everyone was in awe of my enthralling presence. But! An evil golden-haired bitch (whoops, I meant witch) appeared and ruined my outfit! Distraught. Unethically mistreated. Heartbroken and despaired, I fled from the Ball. It was the darkest night of my soul! All hope for my happily-ever-after was snatched away from me like an innocent fawn snatched away from its mother by a feral blue-eyed beast in an all-white satin jumper (even though it’s clearly after Labor day). Then appeared Daddy Bear, like my knight in shining armor, an owner of a nationwide Business Operation and multiple real estate properties, with the promises of money, love, and the need to make things right. He was a generous, old fashioned, country gentleman, granting me the privilege to live in his cozy rural cabin. Now I am living my fairytale dream with my new unexpected daddy who spoils me with love, affection, and anything my heart desires. Moral of the story: Get like me, you bitches!”

**Author's Note:**

> This saga will be a collection of random one-shot stories involving the theme of "sissyboys", but Quinn's story is the only one that will have multiple chapters. 
> 
> This is an experimental series for me, so I'm not sure when I'll be updating these. Just whenever I feel like writing about sissyboys I suppose. 
> 
> But if you have any story ideas involving sissyboys that you would like me to try my hand at, let me know, and I'll see what I can do!
> 
> -Kono


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